N-(n-dodecyl)-n-(3,4-dichlorophenethyl)-n, n-dimethyl-ammonium compounds



Patented Dec. 29, 1953 2 5 4 444 UNITED STATES PATENT ()FFICE N-(ln-DODECYL) N (3,4 DICHLOROPHEN- ETHYL) N,N DIMETHYL AMMONIUM COMPOUNDS No Drawing. Application November 20, 1951,

Serial No. 257,425

3 Claims. (Cl. 260-5675) 1 2 This invention relates to N-(ndodecyl)-N- EXAMPLE 1 (3,4-dichlorophenethyl) N,N dimethylammo- N (n dodec yl) -N- (3,4-dzchlorophenethyl) mum salts having the formula N,N-dimethylammom'um bromide where An is the anion of a strong organic or in- 100 of N"N dimethy1 3, 4 dich1orophen organic acid; and to the preparation of the Same is: ethylamine and 11.4 g. of n-dodecyl bromide The anion in the above formula for my were dissolved in 150 ml. of acetone and the sonew compounqs P for example aniqn lution thus obtained was boiled under reflux for of a hydrohalic acid such as hydrochloric acid four hours The reaction mixture was then or hydrobromic acid p'toluenesulfom? cooled to 0 C. The crystalline product which methyl hydr?gen.sulfate' metthanesulfomc acid is separated from the solution was collected on a ethanesulmmc and filter, washed with ml. of cold acetone and My new compounds exhibit high antifungal acthen with 50 mL of anhydrous ether and then tivity and are also useful as antibacterial agents. dried in a vacuum desiccator over hosphorus The compounds of my invention can in many pentoxide. There was thus obtained 20 g of instances be most conveniently obtained by A} N (n dodecy1) 4 dichlomphenethyn treating dichlorophenethyl dimethylammonium bromide which melted at amine with an ester having the formula (n-do- Q decyD-An. This reaction is represented by the EXAMPLE 2 following equation:

N- (n-dodecyl) -N- (3,4-dichlorophenethyl) GH -(CH2)1!?0HI-AD-i-(CHahN-CHn-CHeQ-CI N,N-dimethylammonium chloride (51 CH: CH:

An I When N,N-dimethyl-3,4 dichlorophenethylamine is heated with n-dodecyl chloride in This procedur is u l f r p Where benzyl alcohol solution in a manner analogous An is Cl-, Br---, CH3SO3-, CzHs-SOaand to the procedure described above in Example 1, p-CH3C6H4SO3- This reaction is advantathere is obtained N-(n-dodecyl) -N-(3,4-dichlogeously carried out by heating appr x m ely rophenethyl) -N,N -dimethylammonium chloride.

equimolecular proportions of the two reactants I claim:

together at about 40-225 C. in an organic sol- 1. A compound having the formula vent and then isolating the desired product by 40 CH3 OH:

cooling the reaction mixture and collecting the product which separates from solution. 3 (CHfiw-CHz-dII-CHaOHzQ-Cl When An is CH3SO4, i. e. when it is desired n I to prepare N-(n-dodecyl) -N-(3,4-dich1or0phen- C1 ethyl) -N,N-d et y amm um ho ulfate. I r where An is the anion of a strong acid.

prefer to treat N-methyl-N-(n-dodecyl)-3,4-di- 2. N-(n-dodecyl) -N-(3,4 dichloroplienethyD- chlorophenethylamine with me hyl sulf teh N,N-dimethylammonium bromide.

reaction proceeds in accordance with the follow- 3. N-(n-dodecyl) -N-(3,4 dichlorophenethyl) ing equation: N,N-dimethylammonium chloride.

cm CHARLES EDWARD KWARTLER. l CH;-(CHl)io-CH2-NCHi*CH 8)' References Cited in the file of this patent 1 UNITED STATES PATENTS Number Name Date CHMcmMH N /CHFCWQg1 as 2.10 .7 5 Domagk Feb. 15, 1938 mom I FOREIGN PATENTS 01 Number Country Date My invention is illustrated by the following ex- 458.033 Great Britain Dec. 8, 1936 amples without, however, being limited thereto. 2 France Sept. 28, 1936 

1. A COMPOUND HAVING THE FORMULA WHERE AN IS THE ANION OF A STRONG ACID. 